Most Helpful Guy
Surgery to lose weight! Why u won't eat less and move more?
Most Helpful Girl
You need to let him know before you guys meet so that there are no surprises.
I know it's an awkward conversation to have, but you just have to be strong, honest and hope for the best. Get all dolled up and take a non-misleading photo of your body. You want him to like you for you, right? Then this is what you have to do, because attraction is important, as is honesty.
Since you guys have developed a pretty strong bond, there is a good chance that he'll appreciate your honesty and not really care. If things do happen to go south, then at least you can free yourself from the burden of hiding your true self (physically-speaking).